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The painted panel illustrates a story in three scenes from left to right. One of the main characters, a young man called Ambrogiuolo, appears several times. Bernabo, a merchant from Genoa has boasted of his wife Ginevra's virtue and bets Ambrogiuolo will not succeed in seducing her. Ambrogiuolo bribes an old woman to have him carried into Ginevra's bedroom hidden in a chest. He is then shown looking at Ginevra. He finds a mole under her left breast and will use this information to convince Bernarbo of his mission's success. The rest of the cassone (chest) is a nineteenth-century reconstruction.

Toscani is best known as a cassone painter, that is, a painter of decorative panels on the sides of large wooden chests or cassoni. These were usually commissioned in pairs for newly married couples and many were produced in Florence from the fourteenth century to the end of the sixteenth century. Like several Florentine painters, Toscani may have worked on the narrative relief panels of the first set of Baptistry doors designed by Lorenzo Ghiberti. He seems to have painted some frescoes and altarpieces in addition to cassoni, in a style influenced by Ghiberti and Lorenzo Monaco.